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21. Sustmann R (1974) Orbital energy control of cycloaddition reactivity. Pure Appl Chem
40:569–593
22. Leihkauf P, Lohse V, Csongar C, Tomaschewski G (1989) Photochemistry of diarylsubstituted
2H-Tetrazoles XI. and sydnones. V. flashphotolytic investigations with 2,5 -Diaryl-2Htetrazoles and 3,4-diarylsydnones. Absolute rate constants of cycloaddition reactions of
diarylnitrile imines to dipolarophiles. J für Prakt Chemie 331:789–798
23. Leihkauf P, Lohse V, Csongár C, Tomaschewski G (1990) Photochemistry of diaryl-substituted
2H-Tetrazoles XII. On the influence of the solvent and the temperature on the cycloaddition
rate constants of diarylnitrilimines on dipolarophiles. Zeitschrift für Chemie 30:29–30
24. Wang Y, Song W, Hu WJ, Lin Q (2009) Fast alkene functionalization in vivo by photoclick
chemistry: HOMO lifting of nitrile imine dipoles. Angew Chem Int Ed Engl 48:5330–5333
25. Eckell A, Huisgen R, Sustmann R, Wallbillich G, Grashey D, Spindler E (1967) 1.3dipolare cycloadditionen, XXXI. Dipolarophilen-Aktivitäten gegenüber Diphenylnitrilimin
und zahlenmäßige Ermittlung der Substituenteneinflüsse. Chem Ber 100:2192–2213
26. Kurra Y, Odoi KA, Lee Y-J, Yang Y, Lu T, Wheeler SE, Torres-Kolbus J, Deiters A, Liu
WR (2014) Two rapid catalyst-free click reactions for in vivo protein labeling of genetically
encoded strained alkene/alkyne functionalities. Bioconjug Chem 25:1730–1738
27. Yu Z, Lin Q (2014) Design of Spiro[2.3]hex-1-ene, a genetically encodable double-strained
alkene for superfast Photoclick Chemistry. J Am Chem Soc 136:4153–4156
28. An P, Wu H-Y, Lewandowski TM, Lin Q (2018) Hydrophilic azaspiroalkenes as robust
bioorthogonal reporters. Chem Commun 54:14005–14008
29. Sato E, Kanaoka Y, Padwa A (1982) Intramolecular photocycloaddition reaction in the 2-(4pentenyl)-5-aryl-Substituted tetrazole system. J Org Chem 47:4256–4260
30. Wang XS, Lee Y-J, Liu WR (2014) The nitrilimine-alkene cycloaddition is an ultra rapid click
reaction. Chem Commun 50:3176
31. Huisgen R, Seidel M, Sauer J, McFarland J, Wallbillich G (1959) Communications: the
formation of nitrile imines in the thermal breakdown of 2,5-disubstituted tetrazoles. J Org
Chem 24:892–893
32. Tanaka K, Maeno S, Mitsuhashi K (1982) Preparation of trifluoroacetonitrile phenylimine
and its reactions with some dipolarophiles. Chem Lett 11:543–546
33. Baruah KA, Prajapati D, Sandhu JS (1988) Studies in chromone derivatives: cycloaddition
Reactions of 4-oxo 4H-1-benzopyran-3-carboxaldehyde Imines with benzonitrile oxide and
nitrilimine of 4-oxo-4H-1-benzopyran-3-carboxaldehyde with alkenes. Tetrahedron 44:1241–
1246
34. Barzaghi M, Beltrame PL, Dalla Croce P, Del Buttero P, Licandro E, Maiorana S,
Zecchi G (1983) Regioselectivity of 1,3-Dipolar cycloadditions of (Phenylsulfinyl)- and
(Phenylsulfonyl)alkenes. J Org Chem 48:3807–3810
35. Padmavathi V, Reddy BJM, Reddy BCO, Padmaja A (2005) Synthesis of a new class of
keto-linked bis Heterocycles. Tetrahedron 61:2407–2411
36. Yavari I, Taheri Z, Naeimabadi M, Bahemmat S, Halvagar M (2018) A convenient synthesis of
Tetrasubstituted Pyrazoles from Nitrile Imines and 2-(Thioxothiazolidin-5-ylidene)acetates.
Synlett 29:918–921
37. Fusco R, Garanti L, Zecchi G (1974) Intramolecular cycloadditions of nitrilimines on
acetylenic groups. Tetrahedron Lett 15:269–272
38. Garanti L, Sala A, Zecchi G (1977) Intramolecular 1,3-dipolar cycloadditions of nitrile imines
bearing an alkenyl substituent. J Org Chem 42:1389–1392
39. Pla D, Tan DS, Gin DY (2014) 5-(Methylthio)tetrazoles as versatile synthons in the
stereoselective synthesis of polycyclic pyrazolines via photoinduced intramolecular nitrile
imine-alkene 1,3-dipolar cycloaddition. Chem Sci 5:2407–2415
40. Meier H, Heimgartner H (1985) Intramolekulare 1,3-dipolare Cycloadditionen von
Diarylnitriliminen aus 2,5-Diaryltetrazolen. Helv Chim Acta 68:1283–1300
41. Basolo L, Beccalli EM, Borsini E, Broggini G, Khansaa M, Rigamonti M (2010) Access
to a novel class of tetracyclic 1,4-Benzodiazepin-5-ones starting from α-amino acids by Pdcatalyzed amination/1,3-dipolar cycloaddition as the key steps. Eur J Org Chem 2010:1694–
1703
87
21. Sustmann R (1974) Orbital energy control of cycloaddition reactivity. Pure Appl Chem
40:569–593
22. Leihkauf P, Lohse V, Csongar C, Tomaschewski G (1989) Photochemistry of diarylsubstituted
2H-Tetrazoles XI. and sydnones. V. flashphotolytic investigations with 2,5 -Diaryl-2Htetrazoles and 3,4-diarylsydnones. Absolute rate constants of cycloaddition reactions of
diarylnitrile imines to dipolarophiles. J für Prakt Chemie 331:789–798
23. Leihkauf P, Lohse V, Csongár C, Tomaschewski G (1990) Photochemistry of diaryl-substituted
2H-Tetrazoles XII. On the influence of the solvent and the temperature on the cycloaddition
rate constants of diarylnitrilimines on dipolarophiles. Zeitschrift für Chemie 30:29–30
24. Wang Y, Song W, Hu WJ, Lin Q (2009) Fast alkene functionalization in vivo by photoclick
chemistry: HOMO lifting of nitrile imine dipoles. Angew Chem Int Ed Engl 48:5330–5333
25. Eckell A, Huisgen R, Sustmann R, Wallbillich G, Grashey D, Spindler E (1967) 1.3dipolare cycloadditionen, XXXI. Dipolarophilen-Aktivitäten gegenüber Diphenylnitrilimin
und zahlenmäßige Ermittlung der Substituenteneinflüsse. Chem Ber 100:2192–2213
26. Kurra Y, Odoi KA, Lee Y-J, Yang Y, Lu T, Wheeler SE, Torres-Kolbus J, Deiters A, Liu
WR (2014) Two rapid catalyst-free click reactions for in vivo protein labeling of genetically
encoded strained alkene/alkyne functionalities. Bioconjug Chem 25:1730–1738
27. Yu Z, Lin Q (2014) Design of Spiro[2.3]hex-1-ene, a genetically encodable double-strained
alkene for superfast Photoclick Chemistry. J Am Chem Soc 136:4153–4156
28. An P, Wu H-Y, Lewandowski TM, Lin Q (2018) Hydrophilic azaspiroalkenes as robust
bioorthogonal reporters. Chem Commun 54:14005–14008
29. Sato E, Kanaoka Y, Padwa A (1982) Intramolecular photocycloaddition reaction in the 2-(4pentenyl)-5-aryl-Substituted tetrazole system. J Org Chem 47:4256–4260
30. Wang XS, Lee Y-J, Liu WR (2014) The nitrilimine-alkene cycloaddition is an ultra rapid click
reaction. Chem Commun 50:3176
31. Huisgen R, Seidel M, Sauer J, McFarland J, Wallbillich G (1959) Communications: the
formation of nitrile imines in the thermal breakdown of 2,5-disubstituted tetrazoles. J Org
Chem 24:892–893
32. Tanaka K, Maeno S, Mitsuhashi K (1982) Preparation of trifluoroacetonitrile phenylimine
and its reactions with some dipolarophiles. Chem Lett 11:543–546
33. Baruah KA, Prajapati D, Sandhu JS (1988) Studies in chromone derivatives: cycloaddition
Reactions of 4-oxo 4H-1-benzopyran-3-carboxaldehyde Imines with benzonitrile oxide and
nitrilimine of 4-oxo-4H-1-benzopyran-3-carboxaldehyde with alkenes. Tetrahedron 44:1241–
1246
34. Barzaghi M, Beltrame PL, Dalla Croce P, Del Buttero P, Licandro E, Maiorana S,
Zecchi G (1983) Regioselectivity of 1,3-Dipolar cycloadditions of (Phenylsulfinyl)- and
(Phenylsulfonyl)alkenes. J Org Chem 48:3807–3810
35. Padmavathi V, Reddy BJM, Reddy BCO, Padmaja A (2005) Synthesis of a new class of
keto-linked bis Heterocycles. Tetrahedron 61:2407–2411
36. Yavari I, Taheri Z, Naeimabadi M, Bahemmat S, Halvagar M (2018) A convenient synthesis of
Tetrasubstituted Pyrazoles from Nitrile Imines and 2-(Thioxothiazolidin-5-ylidene)acetates.
Synlett 29:918–921
37. Fusco R, Garanti L, Zecchi G (1974) Intramolecular cycloadditions of nitrilimines on
acetylenic groups. Tetrahedron Lett 15:269–272
38. Garanti L, Sala A, Zecchi G (1977) Intramolecular 1,3-dipolar cycloadditions of nitrile imines
bearing an alkenyl substituent. J Org Chem 42:1389–1392
39. Pla D, Tan DS, Gin DY (2014) 5-(Methylthio)tetrazoles as versatile synthons in the
stereoselective synthesis of polycyclic pyrazolines via photoinduced intramolecular nitrile
imine-alkene 1,3-dipolar cycloaddition. Chem Sci 5:2407–2415
40. Meier H, Heimgartner H (1985) Intramolekulare 1,3-dipolare Cycloadditionen von
Diarylnitriliminen aus 2,5-Diaryltetrazolen. Helv Chim Acta 68:1283–1300
41. Basolo L, Beccalli EM, Borsini E, Broggini G, Khansaa M, Rigamonti M (2010) Access
to a novel class of tetracyclic 1,4-Benzodiazepin-5-ones starting from α-amino acids by Pdcatalyzed amination/1,3-dipolar cycloaddition as the key steps. Eur J Org Chem 2010:1694–
1703